Orange-red dye and process of making same.



PATENT FFICE.

FRANZ SOHOLL, OF HOOl-IST-ON-TI-lE-MAIN, GERMANY, ASSIGNOR TO THE FARBWERKE, VORM. MEISTER, LUOIUS dc BRUNING, OF IIOOHST-ON-THE- MAIN, GERMANY, A CORPORATION OF GERMANY.

ORANGE RED DYE AND PROCESS OF MAKING SAME.

SPECIFICATION forming part of Letters Patent No. 695,238, dated March 11, 1902.

Application filed December 21, 1900. Serial No. 40,672. (Specimens) To all whom it may concern:

Be it known that I, FRANZ SOHOLL, Ph. D., a citizen of the German Empire, and a resident of Hochst-on-the-lVlain, in the German Empire,

5 have invented certain new and useful Improvements in Orange-Red Dyes and Processes of Making Same, of which the following is a specification.

I have found that a series of orange-yellow I to orange-red mordant dyestuffs may be obtained if -pyrazolone and its derivatives, bein g non-substituted in the fourth position, are combined with the diazo compounds of orthoamidophenol and its derivatives. Most of I 5 these dyestuffs are valuable as acid dyestuffs.

Their fastness, however, is considerably increased by the formation of lakes. The chrome-lake is formed either by dyeing goods previously mordanted or by subsequent treatzo ment with ohromium-fluorid or bichromate.

The lake-dyes meet every requirement as regards fastness. Of the pyrazolone derivatives as combining substances phenylmethylpyrazolone and its sulfonic acid generally yield 2 5 yellower tints and the pyrazolones containing the carboxyl group redder ones. Of the diazo compounds of the amidophenol derivatives those of the nitro-ortho-amidophenolsulfonic acids are particularly valuable for ob- 0 taining red shades.

I illustrate my process as follows:

First.- Twenty-five kilos of 6-nitro-2-a1nidophenol-eL-sulfonate of sodium (German Patent No. 93,443, Friedlander IV, page 765) are dissolved in about five hundred liters of water and diazotized by adding seven kilos of sodium nitrite and twenty-five kilos of hydrochloric acid of thirty-per-cent. strength. The clear diazo solution is slowly run while stirring into a solution of thirty-eight kilos of the di-sodium salt of l-para-sulfophenyl-o-pyrazolone-il-carboxylic acid (Annalen 294:,232) in about two hundred liters of water. After some hours the solution is gently heated, and the dyestuff is salted out by adding commonsalt. It

separates as an orange-brown crystalline powder. The formation of the dyestuff is accelerated by adding when cooling sodium earbonate or sodium acetate.

In the foregoing example 4-nitro'2-amidophenol-G-sulfonic acid may be substituted for 6-nitro-2-amidophenolt-sulfonic acid and equivalent quantities of 1-phenyl-5-pyrazolone-3-carboxylic acid or para-sulfophenyl-3- methyl-5-pyrazolone may be substituted for 1-para-sulfophenyl-5-pyrazol0ne-3-carboxylic acid.

Second. Twenty-five kilos of 4-nitro-2-amidophenol-G-sulfonate of sodium (French Patent No. 280,031) are diazotized as in Example I. The diazo compound thus formed is run While stirring into a solution of nineteen kilos of l-phenyl-3-methyl-5-pyrazolone, twelve kilos of soda-lye of 40 specific gravity, and six kilos of sodium carbonate in about twohundredlitersofwater. Aftersome'hours the solution is gently heated, and the dyestuif is separated by adding a little common salt as a red crystalline powder. In this example 6-nitro-2-amidophenol-et-sulfonic acid may be substituted for d-nitro-Q-amidophenol-6-sulfonic acid.

Having now described my invention, What I claim is- 1. The herein-described process of making mordant dyestuffs, which consists in diazotizing the products of substitution of ortho-amidophenol and combining the diazo compounds thus obtained with substances containing 1- phenyl- 5-pyrazolone, substantially as set forth.

2. As a new product, the orange-red mordant dyestuff, having the formula:

SO Na and obtained by the diazotization of G-nitro- 2-amidophenol-4-sulfonic acid and the combination with para-sulfo-1-phenyl-5-pyrazolone- 3-carboxylic acid, being an orange-brown crys- 10c talline powder, readily soluble in Water to In testimony that I claim the foregoing as an orange-red solution, insoluble in alcohol, my invention I have signed my name in presether, benzene and petroleum, soluble in conence of two subscribing witnesses.

cen trated sulfuric acid to a clear yellow solu- FRANZ SOHOLL. 5 tion, dyeing unmordanted Wool in an acid- Witnesses:

bath red and forming an orange-red chrome- HEINRICH HAHN,

lake, substantially as set forth. ALFRED BRISBOIS. 

